Chicago-born soul queen, [lastfm link_type=”artist_info”]Jennifer Hudson[/lastfm], may be madly in love with her husband, but the 29-year-old singer has seen enough heartbreak and tragedy with her mother, brother, and nephew’s murders to last her a lifetime.

However, when it comes to love, most of Hudson’s songs are more on the positive tip. We did find Five Jennifer Hudson Songs About Heartbreak that we absolutely love, including a heart-wrenching cover of [lastfm link_type=”artist_info”]Gladys Knight and the Pips[/lastfm]’ “Neither One of Us (Wants to Be the First to Say Goodbye).”

Hudson has been through a lot, which makes her live performances even more magical and powerful, especially her free streamingLive on Letterman concert from the Ed Sullivan Theater on June 13th at 9 PM ET. You can watch the entire concert, live right here!

5. “Why Is It So Hard”

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Sometimes you can still be with someone in a relationship, but they make you sad and break your heart a little more each day, like Jennifer Hudson’s lover in “Why Is It So Hard”:

Doesn’t make sense irrational to me/I’m still around though I can’t believe one word that you say/No it don’t make no sense I’m always crying/But I’d cry oceans if you ever went away/But I could never ever feel like this/When the words I love you leave my lips/I mean it when I say I just hate how difficult you make it

4. “Can’t Stop The Rain”

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There are different kinds of heartbreak; sometimes your heart can be broken from losing someone you love, or even knowing a devastating secret that can’t be changed:

I keep on crying, but it doesn’t seem to help at all [seem to help at all]/With every single tear drop, it’s like another raindrop falls/And I would [and I would], if I could [if I could]..but the try would be in vain [the try would be in vain]/Said so matter what I do..I can’t stop the rain.

3. “Don’t Look Down”

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OK, so this song is pretty upbeat, but it’s a perfect “My heart is broken, but it’s time to finally get over it” song:

Broken hearts and broken dreams/Baby nothing’s broken, as it seems/Gotta find a way to let it flow (oh oh)/I know that there’s a higher place to go

2. “Neither One of Us (Wants to Be the First to Say Goodbye)”

Photo by Larry Bussaca//Getty Images

Originally sung by [lastfm link_type=”artist_info”]Gladys Knight and the Pips[/lastfm], Jennifer Hudson tackles this melancholy but completely realistic love song about being with someone for such a long time, falling out of love, and neither one of you having the bravery to admit to a broken heart and defeat:

It’s sad to think we’re not gonna make it/And it’s gotten to the point/Where we just can’t fake it/For some ungodly reason/We just won’t let it die/I guess neither one of us/Neither one of us wants to be the first to say good-bye

1. “Where You At”

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The worst kind of heart-break (in our opinion and maybe Jennifer Hudson’s) is the kind where you’ve given the person ample opportunity to get their stuff together and they just keep on disappointing you:

You said when the storm came/That you would be there with your umbrella to block the rain/And you said you’d protect me/From heartache, pain, lies, loneliness, and misery/You said you’d tear down the walls that were in my way/You promised things would be okay/And I stood there in the freezing cold/And I waited for you, but you never showed

Don’t forget to come back right here, on Monday June 13th at 8 PM ET, to watch Jennifer Hudson Live on Letterman, presented by AT&T!